


.11 It's Never Like That

by LaPilar



Series: Supernatural Imagines/One-Shots [11]
Category: Supernatural
Genre: 18+, Bit of Fluff, Dragons, F/M, Loss of Virginity, NSFW, One Shot, Smut, bit of angst, virgin!reader
Language: English
Status: Completed
Published: 2018-01-12
Updated: 2018-01-12
Packaged: 2019-03-03 17:41:37
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 5,113
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13346232
Author URL: https://archiveofourown.org/users/LaPilar/pseuds/LaPilar
Summary: A bad dream while on a dragon hunt leads you to confess to Dean that your virginity is putting the team at risk, and you'd like him to fix that. He agrees, the gentleman he is.





	.11 It's Never Like That

I shot up in bed in the middle of the night, still terrified despite the fact that I now realized it had all been a dream. A possible dream, probable even, but a dream nonetheless. Sam and Dean were still alive, they hadn't died because of me.  
But that might not be true in a few days. And my muscles wouldn't stop shaking; I couldn't sleep anymore knowing that I was taking that type of risk. So I threw back the covers and shoved my feet into the closest boots, not bothering to even primp myself before I snatched the key off the counter and was out the door.  
Sam and Dean were three doors down; the gentlemen they were, never forced me to share a room with them. I reached their door in seconds and began pounding on it furiously. "Open up, it's me," I called, my voice small and shaky. I kept it low, not wanting to wake any of the neighbors.  
There was muttering cursing from inside, followed by the click of two locks, and I was brought face to face with a jilted Dean. I looked him up and down; my subconscious unable to believe what I had seen was just a dream.  
"What-" he began, but stopped abruptly when I threw my arms around him.  
"You're okay," I breathed, finally letting myself relax against him. You never realize how tense you are until you find release for that tension.  
I could feel the confusion, palpable on his body, and I released him soon after. He looked more confused than ever. "What?" he asked, throwing his arms up in confusion and exasperation.  
Sam appeared over Dean's shoulder, more concerned than annoyed. He squinted against the harsh parking lot lights and asked, "What's wrong?" in a voice that was more sleep than wake.  
I looked at Dean, making a decision in my head then and there. "Can I talk to you alone?"  
This obviously didn't clear things up. The boys exchanged a look, and Sam shrugged. Dean turned back to me and nodded. "Your room?"  
"Sure."  
He gave me a testing look. "Am I coming back here tonight?" He jerked a thumb backwards at his own room.  
"I'm not sure."  
He sighed, turning back to grab the doorknob. "Don't wait up for me," he instructed Sam, who was already heading back to bed.  
Once the door was shut, I grabbed Dean's hand and tugged him back to my room eagerly, now too aware of the chill outside and my skimpy shorts and tank.  
"Slow down, god. What's wrong?" he asked.  
"Nothing's wrong. But I've kinda been hiding a secret from you and Sam and I need to tell you," I explained, pulling out my key and letting myself into my room.  
Dean shut the door behind him and continued, "Okay, so why now?"  
I finally turned and made eye contact, resting the edge of my butt against the small table in the room. "It's crossed my mind that at the moment, it's a secret that may end up getting someone killed or hurt." I left out the detail about the dreams. He didn't need to worry about me being a prophet or clairvoyant on top of everything else.  
This made his eyes go wide. He finally seemed completely awake. "Okay, then spill."  
"And I have a favor to ask of you on top of it. It's kinda weird, but I hope you'll do this for me."  
"Y/N." He said firmly.  
"I don't want to tell you," I finally admitted, letting my eyes slide to the floor as my voice fell.  
He groaned and came over to hold me by the shoulders, forcing me to look him in the eye. "Look, you know Sam and I pretty well. We've fucked up pretty badly over the years. Whatever it is, we'll fix it. I'm not givin' up on you yet."  
I blew out a nervous breath. "Okay. I'm just going to get right to it, I guess. I'm a virgin," I confessed, biting my lip with nerves.  
It took a second for the news to register with Dean. When it did, his grip on my shoulders tightened and frown lines appeared on his forehead. "What?"  
"I think it's pretty obvious what that means," I said, rolling my eyes and shrugging his hands off me. I walked to the bed and folded my legs under me, letting him take in the news.  
"Are you serious?" he asked, a myriad of emotions passing over his face as the repercussions of what I just told him washed over him.  
"Yeah. I know I'm 21, but there was never the right guy at the right time, and I wasn't about to lose it to some douchebag in a bar."  
“That’s..” he seemed to be struggling to find the words. “That’s crazy! You’re 21!”  
I glared at him. "Thanks, that's really helpful."  
"We're hunting dragons!" he seemed to realize out loud.  
"I know. That's kinda why I had to tell you now."  
He shook his head and smacked his cheeks as if trying to wake himself up still. "Okay. Okay, it's going to be fine. Pack your stuff, and we'll get you on a bus back to Kansas, and you can make your way to the bunker from there. Or if you'd rather, you could just hole up in a hotel a state over, we can pick you up on our way through-"  
"Dean," I cut through his ramblings, my cheeks turning red when he finally looked over at me. "I appreciate it, but I don't really want to leave. Besides, that's just avoiding the problem, not solving it. What if I just.. stop being a virgin?"  
He squinted at me in confusion. "That's not how that works?" He said it like a question.  
I sighed in exasperation, moving to sit on the edge of the bed, closer to him than I had been before. He paced the floor in front of me.  
"You mean, just go find some guy in a bar? That sort of thing? I really hate to think that you're losing it to some stranger just because of a hunt, not that it's any different from how mine was, just.."  
"Dean," I said, louder this time. I stood up and walked right over to him, putting my hands on his shoulders and forcing him to look at me. That wasn't the hard part. The hard part was forcing myself to look back at him. "It wouldn't be some random guy."  
I waited, and I could see the lightbulb go off in Dean's mind. He immediately shook his head. "No way. That's crazy."   
He shrugged off my hands, and I let him walk away from me. "Why is it crazy? I know I'm not your type, but you'd be doing me a big favor. I trust you; I want it to be you more than anyone else. It's not like I was trying to wait until marriage or anything. I was waiting for the right time, and this is it." I was rambling, listing off reasons as I started to rethink everything. Maybe I was being crazy.  
"We're a team," he started, turning to give me a hard look that fell somewhere between concern and annoyance. "It'd mess up our dynamic. Sam's going to be pissed, for one. Why me and not him, anyway?"  
"It won't mess up anything. We were friends before, we'll be friends after. Sam wouldn't have to find out, and I can't see him caring if he did." I ignored the last question.  
Dean sighed, long and hard, and I could see he was really thinking about this. "Why me and not Sam?" he finally repeated.  
"I'm closer to you, I trust you more. Sam's more like a brother to me, it'd just be weird. Plus, you're shorter than him? I figured it'd, I don't know, hurt less?" I hadn't meant to say the last part, but there it was.  
He glared at me now. "Wow, thanks. Really makes me feel good about having sex with you that you're already insulting my dick size."  
"That wasn't an insult. I've seen your dick, it's not small by any means. I just figured Sam's would be bigger." I shrugged innocently. Seeing him naked had been an accident a few months ago, a mix-up with bedrooms. We had laughed it off and moved on.  
Dean's face slid into an easy, cocky smile. "Well, thanks."  
I huffed and rolled my eyes. "So?"  
He thought more. "Look, I'm doing you a favor here. I don't want you complaining later saying I took advantage of you or something stupid like that. This is a one-time thing, and it's because you begged."  
He hadn't mean to hurt me, but his words still stung. I straightened up and leaned back, as if I'd been slapped. "Wow, why don't you tell me how you really feel. If it's such a fucking chore maybe I will go ask Sam." I stood up and made for the door, but he intercepted me, grabbing my arm and steering me back to the bed. This time he sat down with me.  
"Look, I didn't mean that as an insult, and you know it. I just want you to really, like 100% want this. Of course I want to have sex with you; that's not a chore at all. I'm a dude." He made a face as if he couldn't believe what I'd just said, and I couldn't help but crack a smile at it. He seemed to relax after I did. "Just to be clear, you've done.. like other stuff, right?"  
"Yeah, I've sucked dick, if that's what you're asking. And made out and done all the other stuff. That's not a problem."  
"Okay. You're sure this is what you want?" he asked again, his gaze leveled on mine.  
This time I didn't struggle with holding it. "Yes."  
"Okay." He stood up and moved over to the blinds, snapping them shut before returning to my side. He leaned against the headboard and wrapped his arms around my waist, pulling me back towards him. I froze up. "Wait, just, just like that? We're going?" I asked, trying to disguise my nerves.  
"God, Y/N, no. I was going to cuddle with you while we discuss terms. That okay?" he asked mockingly.  
"Oh. Yeah." I sat between his legs, and wiggled my shoulders on his chest until they were comfortable. I could feel the soft outline of his dick against my back, but resolved myself to getting used to it. His arms were wrapped around me and he held my hands in his, tracing patterns over the skin there. It was actually nice.  
"So, your terms?" he asked.  
It was easier talking without having to actually look at him. "Uh, get me really turned on first I guess?"  
He chuckled, and I felt it in his chest more than heard it. "That's not going to be a problem, trust me sweetheart." His right hand moved suddenly to rest on the top of my thigh before he slid it down to the inside, right over my heat.  
I jumped first, then took in a sharp breath at the sensation. He laughed again and returned his hand to mine, knowing exactly what he'd done.   
"Also, be gentle with me," I continued.  
"I'll be gentle for as long as you want me to be, but you might end up begging me to be rougher," he said, and it sent shivers through me. His fingers were ghosting up and down my arms now, just the slightest of touches, and it made it hard to breathe for some reason.  
"Also, don't tell Sam. If he finds out somehow, that's okay, but I don't want him to know if he doesn't have to."  
"Agreed. Those your terms?" he asked.  
I thought for a brief moment. "Yep, I think that's it. What about you?"  
"First, be open-minded. If you really don't want to do something, I won't do it obviously, but if we get into different positions or that sort of thing, at least try it unless you have a really compelling reason not to."  
"I can do that. Although it is my first time, so I wouldn't expect too much."  
"You'll be fine. You have a great teacher, after all. Second, if you change your mind or are having any doubts at all, let me know right away."  
"You don't have to worry about that," I reassured him. "I'd never do something I didn't want to."  
"I know, I know. It's just, during things like this, words and meanings can get mixed and sometimes it's hard to know what you really want. We're good though?"  
I nodded. "Yeah. That it?"  
"Not quite." I felt him take a deep breath, and he said, "If at the end of this, we're both happy, and we both want to, promise me we can do this again. Maybe make it some sort of friends with benefits type thing?"  
This made me turn to face him in surprise. The look on his face was like he thought I was about to slap him. "Really?" I asked.  
"Yeah. I mean, I've never slept with the same woman more than a few times, so it might be kinda nice to learn everything about someone and try different things with them. Plus, it'd be nice to have a reliable lay on hunts."  
"Okay. I'm open to that. But Sam would probably find out," I reasoned.  
"We'll cross that river when we get to it. So you happy with our agreements?" he asked, and I moved onto his legs, straddling his lap.  
"Yeah. I'm assuming you are?"  
He grinned. "Let's do this. Wait, do you have condoms?"   
The look on his face was so apologetic it almost made me laugh. "Yeah, of course." I walked over and pulled the box out of my duffel, tossing it on the nightstand as I passed.  
"Good. That really might've told Sam something was up, if I went back to our room to grab those," he joked.  
I laughed and hopped back onto the bed, returning to my position on his legs. "Kiss me, Dean Winchester," I ordered, faking confidence since I couldn't seem to find any of my own.  
He grinned. "Yes ma'am." He took my face in his hands and gently tugged me over to his level, and our lips met.   
He was easy to kiss, and I soon felt myself relaxing against him. I stayed in his lap for a few minutes, just kissing him and running my hands over him. His own started in my hair, then moved down to my shoulders, then from there to my hips, and finally down to the swell of my ass. I was too preoccupied memorizing the planes of his chest to mind. Suddenly, he tugged me forward, making me nearly fall against his chest and causing my crotch to rub directly on his dick.  
I gasped in surprise, my eyes shooting open and surprised to see that Dean had a look of pure bliss over his face. I swiveled my hips over his in experiment, and he sighed a long, satisfied sigh. I chuckled and grabbed his hair, tugging it to the side roughly. He was too relaxed; I needed to keep him on his toes.   
My teeth sank into his soft earlobe, pressing just enough to cause him to jump a little before I released and moved onto his neck. I kissed up and down, giving little bites and tracing them with my tongue. I was careful to keep the pressure light enough that I knew it wouldn't cause hickies.   
"What happened to keeping it gentle?" Dean joked.  
I took a break to answer. "That was for the actual sex. Otherwise, I like it rough."  
I pulled back in time to see his eyes go wide, and his hands gripped the bottom of my tank before pulling it over my head. I was glad to not be wearing a bra. "In that case," he said, and gripped me around the middle before rolling us over with no warning. "I'm in charge," he muttered, before taking to my neck. He took a fistful of hair in his hand and tugged straight down, so I was forced into looking at the headboard. I moaned as he sucked at my neck first, slowly making his way down to my breasts. He kissed all over first one, than the other, before taking my right nipple in his fingers and tugging on it. I gasped and squirmed, although I wasn't sure if I was trying to get further from or closer to him.   
My hips jumped up when he set in on the other one, but he kept them pinned down under his own. "Shh," he murmured. "Wouldn't want Sammy to come investigating, would we?"  
"I don't know," I said breathlessly. "Could be kinda hot." I offered him a mischievous grin, and he shook his head in disbelief.  
"We'll talk about that later. I can't believe you're a virgin with a filthy mouth like that. Come suck me off." He flopped himself down with his head on a pillow, and I tore his shirt off before making quick work of his shoes, socks, and jeans. He has pretty hard by the time I kissed him again, making my way down his chest and stomach before tugging his boxers down just enough to let his dick come out. I took to my job with fervor, working up and down his dick like it was my job and letting the obscene, sucking noises of a good blowjob fill the room. Dean seemed happy, as he groaned and grabbed my head. I let him control the speed, but soon he was pulling me up and off of him. "Look, you're great at that, but I'm going to cum in your mouth soon if you're not careful. Let me do some work for a bit," he said, but didn't move to sit up.  
When I gave him a questioning look, he grinned and crooked a finger towards me. "Ride my face, Y/N."  
I wasn't about to turn down that offer. I stepped off the bed and tore off my shorts. "God you're gorgeous," he muttered, and I turned to see him rubbing himself slowly at the sight of me naked.  
"You're not too bad yourself," I teased, tugging his boxers completely off and French kissing him. I took the opportunity to grind my very wet pussy against his equally hard dick, and he grabbed my arm, squeezing it almost painfully. When I looked down, his eyes were half-closed and his mouth was half-open.  
"C'mon, ride me. Not wet enough," he murmured, grabbing my thighs and tugging me forward. I giggled and made my way into position, hovering over his face. It crossed my mind to be self-conscious, but it was a bit late for that, and Dean was looking at me like the dessert he had been cheated out of.   
He pressed two quick kisses to my thighs before surprised me by yanking me down onto him. I yelped in surprise, then again in pleasure when his tongue went to work right away.  
"Fuckkkk," I moaned, letting my eyes slide shut and gripping the headboard to steady myself. I found myself grinding down on Dean, and though I tried to keep most of my weight off him, he didn't seem to mind. I hadn't thought I could get much wetter. I had been wrong. I felt Dean shift a bit to crook a finger inside me, and I instinctively clenched around it.  
He took a break to say, "You taste so good. Tell me when it starts to hurt."  
I wasn't quite sure what he meant, but he slid a second finger into me when he resumed his work. It took a second, but I adjusted to that one too. It was only when he added a third finger that it began to sting.  
"Shit," I murmured, squinting my eyes in pain and pleasure.   
He must've sensed the change in my tone, because he took another break to advise me to, "Relax, sweetie. Don't think about it."  
I took a deep breath and forced my muscles to relax around him, and the pain subsided. He began working his fingers in and out of me, slowly at first then faster as my moans picked up from his tongue on my clit. I focused on that oh-so-lovely feeling spiraling up inside me, letting my eyes slide shut and unable to keep most of weight off him anymore as his mouth and hands wreaked absolute havoc on me.   
"Dean, I'm gonna cum," I managed to get out, but he just kept right on going. It had come on so quick, quicker than ever before, but then again Dean was no ordinary lover.   
I came with a loud moan, and I could've sworn my vision went black for a second. Only Dean's arms holding them apart preventing my thighs from squishing his head. He kept me firmly planted on him, and gave me little kitten licks as my breathing softened and things returned to normal.  
"Okay, okay," I finally said, sitting up on wobbly legs to let him wiggle out from under me. I fell back on the bed after that, still twitching occasionally and taking shaky breaths.  
Dean smiled slyly as he hovered above me. I could still see the glistening wetness I had left on his chin and nose, and as he lowered himself over me I leaned up and licked him clean, letting out a sigh as I laid back down. "How was that?" he asked.  
"Amazing." I smiled, then fell into a fit of giggles.   
It made Dean frown. "What? Don't laugh at me."  
"I'm sorry, it's not that I promise. You just made me feel.. fucking euphoric. I feel like I'm floating."  
He chuckled and pressed a kiss to my forehead. "That's what Dean Winchester does to girls. You never believed me before, now you know."  
"Yes, now I know. Can we get to the main event?" I asked impatiently, wiggling my hips beneath him. He was rock-hard, I could feel it at the apex of my thighs, and I spread them wide in anticipation.  
He didn't answer, instead rolling his hips against mine. His dick hit my clit, making me shudder. "Eager, huh?" he murmured, continuing his teasing thrusts.  
My breath hitched. "God damnit Dean, please. I need it."  
He smiled down at me. This had to be hard for him too, but he was so much better at pretending it wasn't. "What do you need? Ask nicely."  
"I need you to fuck me. Please," I begged, too far gone to care about my bruised ego.   
"Get a condom," he instructed.   
I did as told, tearing open the foil packaging and handing him the latex. He sat up from me for a second to put it on, then took one of my legs in each hand and spread them as wide as he could. Luckily, I was more flexible than I had thought. He moved back into position, leaving me to keep my legs open and giving me a quick kiss. "Just, try to relax. I know it's exciting to be getting to fuck a Winchester, but we're going to take this slow, okay?" he teased.  
Despite my shivering in anticipation and worry, I nodded. I kept my eyes on his as he lined himself up and started pushing in. I immediately tensed up at the new feeling, but forced myself to relax. Dean paused a second before continuing, and said, "Well, you're definitely tight sweetheart, that's for sure." With a grunt, he pushed a bit further in. That was when it began to hurt. Not a stinging pain or anything too bad, just what you'd imagine. The feeling of a muscle being stretched to its limit for the first time. I squeezed my eyes shut and focused on breathing, focused on relaxing. A final groan from Dean, and he was all the way in. I let out a whimper at the feeling, my eyes still screwed up against the uncomfortable new sensation.  
"Y/N, look at me," Dean said, gently but firmly, and I opened my eyes slowly, surprised to see his own eyes half-closed and his bottom lip caught between his teeth. He looked to be enjoying this a hell of a lot more than he'd thought he would. "That's better," he said, seeming to let out a breath. "How do you feel?"  
"It's getting better," I said, the truth.  
He dipped his head and kissed my neck again, gently this time, and the feeling of his scruff on me sent a shiver through me. His soft attentions took the focus off the pain, and I soon said, "Please move."  
He didn't ask anything else, just pulled half the way out, slowly, and slammed back home. And it really was a slam, I don't think he'd meant to, but it looked like he just couldn't help himself. It didn't hurt though. "God," he moaned, letting out a filthy chuckle through clenched teeth. "You've got to be the tightest girl I've been with in ages. You feel so fucking good."  
It gave me confidence, even in such a new and strange situation. "Move, Dean, please," I repeated, wrapping my arms around his lower back and encouraging him out, then back in again. This time, he didn't stop. He set up a slower pace, giving me time to adjust.  
"How ya' feeling, sweetheart?" he asked, breathlessly, eyes still half-shut and taking in deep swallows of air.  
"So much better." I let out a little moan, clawing at his back as I wanted more of him, and faster. The pain had finally completely segued into pleasure; I was surprised at how immediate the change had been.   
He finally reached what seemed to be the maximum speed he was willing to do. Not that it was slow by any means of the word. I was bouncing up and down on the bed, my breasts flying wildly and only his hands above my shoulders keeping him inside me.   
"Dean," I moaned, letting my eyes slide shut with pleasure. This time, he didn't protest.  
"So, fucking, good, Y/N," he managed.   
I was taken by surprise then, when he wrapped his arms around my back out of the blue and rolled us so that I was on top. I gasped as the roll changed our angle, and he didn't even give me a chance to stop as he grabbed my hips firmly and guided me up and down on the dick. It didn't take me too long to fall into a rhythm, and his hands went behind his head as he smiled proudly at me. "I'm an amazing teacher," he said.  
I scoffed and swatted him on the chest. "Maybe I'm just a quick learner."  
"Let's call it a compromise, sweetheart. No point arguing about good sex." I slammed down on him particularly hard then, and he let out a loud groan before letting his right thumb snake around to rub my clit. Soon, I was the one moaning.   
"My turn again," he finally said. I had no complaints; I was soaked in sweat and panting by that point. He pulled me off him and stood up off the bed, flipping me onto my stomach and yanking me towards the side of the bed. I stood on my tiptoes, resting my hips against the edge of the bed, and Dean slammed into me from behind. The depth he got made me go cross-eyed for a second. I liked being on top, but he could go so much faster like this, and when he took my hair in his hand and pulled back, forcing me to look at him, I knew without a doubt this was my favorite position. His other hand reached down to rub my clit again, and I moaned wantonly, hoping against all hopes that the neighbors were heavy sleepers.   
"You close?" Dean asked, his own voice heavy with lust. His thrusts were beginning to stutter, and I sensed this was the beginning of the end.  
"Uhhh, uh-uh," was all I could manage. I looked back again to meet his gaze, those electric green eyes seeming like they could pierce straight into my soul. I suddenly understood why guys liked eye contact during blowjobs.   
Only a few moments later, my eyes squeezed shut and my hips rolled back to meet Dean's a few times as I stuttered Dean's name and came violently, my whole body shuddering. Only his hands on my hips kept me in place, and with a few more thrusts he came with a grunt. "God," he groaned a few seconds later, letting himself slide out of me. There was a slight pinch at the sudden absence, but Dean's hands across my back and running through my hair helped calm me down. I found that I couldn't trust me own two feet, and Dean seemed to understand. He picked me up and tossed me onto the bed, going to the bathroom for a few seconds to discard the condom.   
When he came back, I had that same dopy, euphoric smile on my face, and he wore a similar one. "Scooch," he commanded, and I obeyed numbly, letting him pull back the sheets and slide under them, then tug them over the both of us. He laid on his back, and I flopped an arm over his chest, sliding over to rest the side of my head on his still-heaving chest. He right arm wrapped around my shoulders and came to rest on my waist, rubbing comforting circles on the hot skin there.  
"Is it always like that?" I asked, leaning up to press a kiss to the bottom of his jaw in my post-coital bliss.  
"Very rarely is it like that," he responded, sounding as satiated as I felt. "Especially the first time," he added as an afterthought.  
"So about the repeat performance thing. I think we're going to need showers tomorrow, right?" I said, my voice taking on a mischievous tone.  
"Definitely. But for right now, sleep. The dragons won't be coming after you or me or Sam anymore," he assured me, pressing a kiss to the top of my head.   
I fell into a deep slumber easily, exhausted from the night's activities and with no more nightmares to keep me up. And with the promise of more sex with Dean Winchester looming on the horizon.


End file.
